Flat iron your hair.
AKA, straighten it with a ceramic hair staightener.
It takes, what, a few minutes, and virtually every single "celebrity" male with hair longer than a crew does it. It's not just about making your hair obey what you want it to do, it also makes hair shinier and glossier.
Suggested styling examples (for beginners - browse):
http://www.americanidol.com/style/hair/

I love loose fitted beanies - especially hand knitted, or custom designed.
The best ones are usually found in obscure fashion stores downtown - you know, the ones that are usually run by one or two people, and are constantly on the verge of bankruptcy.

Quote:
Originally Posted by DocHolliday
First and foremost, wear comfortable shoes if you'll be doing a lot of walking.
...
Do you own a blazer already? How much of this would you need to buy? (If shoes are on the purchase list, refer to paragraph 1 and make sure you break them in before the trip.)
Agree x2.
Also, street fashion is hot right now. But don't attempt the hobo fashion, where you just mix and match random apparel.
Do loads...